592-51-8Relevant articles and documents
A convergent approach to indolines and indanes
Ly, Thi-My,Quiclet-Sire, Beatrice,Sortais, Benoit,Zard, Samir Z.
, p. 2533 - 2536 (1999)
Radical addition of a xanthate to an N-allylanilide or to a substituted 4-aryl-1-butene followed by cyclisation onto the aromatic ring provide the corresponding indoline or indane respectively.
Rational design of efficient steric catalyst for isomerization of 2-methyl-3-butenenitrile
Han, Minghan,Liu, Kaikai,Wang, Tiefeng
, (2020/10/22)
The catalytic isomerization of 2-methyl-3-butenenitrile (2M3BN), a model reaction in the DuPont process, has been performed using NiL4 (L=tri-O-p-tolyl phosphite) as a catalyst. The lowered catalytic activity in the isomerization with coexistence of 2-pentenenitrile (2PN) and 2-methyl-2-butenenitrile (2M2BN) indicates that both 2PN and 2M2BN are the catalyst inhibitors, and the quantitative relationship between the conversion of 2M3BN and the content of 2M2BN and 2PN is provided. DFT calculation results suggest that the inhibition effect is attributed to the generation of dead-end intermediates (2PN)NiL2 and (2M2BN)NiL2, both of which take nickel atom out of the catalytic cycle in the isomerization process. To suppress the inhibition effect, new catalytic intermediates are rationally designed based on their computational %Vbur. An efficient method that adding extra ligand 1, 5-bis(diphenylphosphino)pentane (dppp5) to the NiL4 catalyst is selected experimentally. Compared to the results obtained with NiL4 as catalyst, the (dppp5)NiL2 increases the conversion of 2M3BN from 74.5 % to 93.4 % at 3 h of reaction and provides a high selectivity to 3PN (> 98 %) at optimal conditions.
I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond
Wang, Sheng,Zhang, Xiaowei,Cao, Chengyao,Chen, Chao,Xi, Chanjuan
supporting information, p. 4515 - 4519 (2017/10/13)
A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.
